The Adventure That Led Me Back to Myself

When was the last time you did something adventurous that scared you just enough to remind you who you are?

For me, the answer came at fifty-one years old.

After leaving a career that had defined me for twenty-seven years, I booked a solo trip to Madeira Island, Portugal, for twenty-one days. Everyone assumed I was going for the hikes. The solitude. The reprieve. Truthfully, so did I.

Armed with nothing more than a suitcase, a journal, and the feeling that something inside me was calling, I boarded the plane alone.

One morning before sunrise, I set out with a local guide, João Caldeira of Heaven on Earth, to hike Pico Ruivo, the highest mountain in Madeira, rising 1,862 metres above the island. Before we headed there, however, he decided to test me. We scaled the side of a mountain above the ocean, holding onto a rope and, it felt like, my life!! He never pressured us. He simply went first and once I’d worked through my fear, I followed.

Like most people, I thought the goal was to reach the summit.  Instead, the mountain became a mirror.

For the first time in years, I wasn’t wearing makeup. I wasn’t dressed for a meeting or introducing myself by my career. I wasn’t multitasking between emails, Microsoft Teams messages, and everyone else’s needs. There were no expectations to perform, achieve, or prove anything.

There was just… me.

With every step, another layer of who I thought I needed to be began to fall away. Somewhere between the clouds and the rocky trails, I stopped focusing on who I had been and started reconnecting with who I was becoming. That lesson stayed with me for the rest of my trip.

I learned how to surf at Around Freedom Surf School, spending far more time falling into the Atlantic Ocean than standing on my board. Every wipeout reminded me that joy doesn’t require perfection. The instructors were endlessly patient, reminding me that we don’t have to do everything alone. And it’s best when we get out of our head.

I struck up conversations with complete strangers in cafés, on hiking trails, and while waiting for buses. It was also the first time I had ever taken public transportation alone in a foreign country. Conversations unfolded effortlessly and not because I had become more interesting, but because I had become more present.

Then something unexpected happened. The more I trusted myself, the more people seemed to trust me.

A local family welcomed me into their home as though I were one of their own. We shared treats, stories, and laughter that no travel itinerary could have planned. One afternoon, a ninety-two-year-old man stopped me on the street simply to tell me that I looked happy.  

“Angelic,” he said.

Me? Angelic?

How could that possibly be?

Those moments reminded me that genuine connection isn’t built through impressive résumés or carefully curated appearances. It begins when we allow ourselves to simply be human. Looking back, I realize I wasn’t climbing a mountain at all.  I was finding my way back to myself.

This trip wasn’t about hiking. It was about removing the masks I didn’t even realize I was wearing. The title, the polished image, the pressure to have everything figured out, and the need to always be planning the next thing.

Without them, people didn’t see a corporate leader. They simply saw Cindy from Canada. And in return, I saw them. There was no competition. No comparison. Only the quiet beauty of nature and the gift of being fully present with another human being.

Looking back, I don’t think it was a coincidence. As I began trusting myself, the people around me seemed to trust me too. The more authentic I became, the more authentic our conversations became. Perhaps when we stop hiding behind who we think we should be, we quietly give others permission to do the same.

Madeira changed me. Yes, because of its mountains. Yes, because of its breathtaking coastline. Yes, because of the Portuguese tarts. But mostly because it gave me the space to remember the parts of myself that had been buried beneath years of responsibility and achievement. It reminded me that grace isn’t found in having all the answers but in allowing yourself to grow through new adventures.

You don’t have to fly across the world or climb Portugal’s highest mountain to experience your own adventure. Maybe yours is taking a class you’ve always wanted to try. Maybe it’s travelling somewhere you’ve never been. Maybe it’s saying yes to something your heart has been quietly calling you toward.

Don’t wait for perfect. The most meaningful adventures rarely begin that way. They begin with the courage to take the first step. You might just find your way back to yourself too.